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  • Title: Total synthesis of gelsemoxonine.
    Author: Shimokawa J, Harada T, Yokoshima S, Fukuyama T.
    Journal: J Am Chem Soc; 2011 Nov 09; 133(44):17634-7. PubMed ID: 21980918.
    Abstract:
    The first total synthesis of gelsemoxonine (1) has been accomplished. Divinylcyclopropane-cycloheptadiene rearrangement of the highly functionalized substrate was successfully applied to assemble the spiro-quaternary carbon center connected to the bicyclic seven-membered core structure. A one-pot isomerization reaction of the α,β-unsaturated aldehyde to the saturated ester via the TMSCN-DBU reagent combination allowed a facile diastereoselective introduction of the latent nitrogen functionality of the unique azetidine moiety.
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